There’s an air of romance to waterfront cities, whether they’re located on oceans, rivers, or lakes. I’ve been a kayak guide on the California coast for 27 years, and paddling on the waterways of major U.S. cities is among my favorite activities to do when I visit.
Looking at the city from the water gives you the chance to enjoy an underrated, less-crowded alternative for admiring the city than driving or walking through its streets. The next time you’re in one of these seven urban areas, rent a kayak or join a guided tour for memorable panoramas.
Austin
Lady Bird Lake, a reservoir on the Colorado River, has no motorized boat traffic, so it’s an ideal place to enjoy time on the water with a view of the Austin skyline. There are eight official access points to the Lady Bird Lake Paddling Trail, which stretches for 11 miles from Redbud Trail to Festival Beach Loop.
Several outfitters have rental kayaks and gear, including the Texas Rowing Center, EpicSUP, Zilker Park Boat Rentals, and Rowing Dock. The Dock also offers a seasonal (June–October) guided paddle to the Congress Avenue Bridge to watch more than 1.5 million Mexican free-tailed bats flying overhead.

The Chicago River also has a riverwalk travelers can explore.
Photo by John Benitez
Chicago
Admire Chicago’s vast skyscraper canyon and the surrounding architecture from a kayak on the Chicago River. The busy waterway has been a means of transportation for generations, and kayak businesses include Urban Kayaks at the Riverwalk, Wateriders at the Kinzie Street Bridge, and Kayak Chicago on the north branch of the river. All three offer rentals with gear, as well as guided tours where you can learn about the city’s architecture and history. Get on the water at sunset or twilight for the best views.
Milwaukee
The Milwaukee Urban Water Trail connects the “urban” portion of the city’s three rivers: Milwaukee, Menomonee, and Kinnickinnic. Summer and early fall are appealing times to leisurely explore the waterways of Milwaukee, soaking in the sun and stopping for tasty dockside bites. Get your boat and gear rentals at Milwaukee Kayak Company, Brew City Kayak, or Milwaukee Kayak Tours. The latter also operates the Cheese Curd Tour, a combination kayaking/walking tour featuring a variety of cheesy delights. Because everyone needs the proper amount of fuel for a truly enjoyable paddle experience.

Head to New Orleans and explore a bayou, which is a swampy part of a larger body of water.
Photo by Rita Harper
New Orleans
If your image of a bayou consists of a misty swamp with trees draped in Spanish moss, head to Bayou St. John on your next trip to the Crescent City. The popular Big Easy Bayou Tour with Kayak-iti-Yat travels from one neighborhood to the next in this midcity bayou, tracing the region’s architecture styles from West Indies–style homes of the 18th century to more modern buildings. Experienced paddlers can choose to go double the distance on the Pontchartrain Paddle tour, a four-hour journey along the length of Bayou St. John, and learn about the area’s diverse ecosystems.
Portland, Oregon
The Willamette River flows through downtown Portland before its confluence with the Columbia River at the northwest edge of the city. Get to know the region better by renting a kayak from Alder Creek Kayak & Canoe at its Jantzen Beach location, where the Columbia splits around Hayden Island, a preferred paddle spot for kayakers with prior experience. Another option is to get a take-away rental from Alder Creek or Next Adventure, where you can strap a kayak to your vehicle’s roof rack or truck bed and launch the kayak from Sellwood Riverfront Park to paddle around Ross Island.
San Francisco
Get an incredible view of the Golden Gate with a paddle trip in San Francisco Bay. With more than 500 square miles of navigable waters, the Bay and its tributaries have kayak outfitters with key locations for spectacular views of San Francisco. For visitors who want to get up close, rent a boat from City Kayak. Die-hard baseball fans can paddle to McCovey Cove, next to the San Francisco Giants’ home in Oracle Park. North of the Golden Gate Bridge in Sausalito, Sea Trek offers rentals and guided trips in Richardson Bay, with its romantic vista of San Francisco.

The Potomac separates Washington, D.C. from Virginia.
Photo by Orhan Cam/Shutterstock
Washington, D.C.
Once the warm weather of spring and summer arrives, explore the nation’s capital from the District’s two rivers, the Potomac and the Anacostia. (History reminder: During the American Civil War, the Potomac River was a boundary between the Union and the Confederacy.) Snag a rental kayak from Boating in DC at any of a handful of locations: Ballpark Boathouse near Nationals Stadium, Fletcher’s Cove Boathouse located upriver from Georgetown, Key Bridge Boathouse in Georgetown, Thompson Boat Center in Georgetown’s Washington Harbor, and the Wharf Boathouse on D.C.’s southwest waterfront. The company also offers seasonal tours to enjoy the cherry blossoms from a watery angle.